Is It Time For a Timeshare?

I have to start with a little admission, I am one of those people who have used timeshare companies for a lot of free weekends. It started even before I was married some 19 years ago. Somehow I convinced my then girlfriend to go with me to Mexico using air miles and all she had to do was sit through a 45 minute presentation. She agreed to go, and by the time we left that 45 minute presentation two and half hours later, we agreed to never do that again. I was just happy she didn’t ask for the next flight home.
A couple years later another company called, we bit and off to Vegas we went. By the time we left that 45 minute presentation two and half hours later, we agreed to never do that again.

A couple years later another company called, we bit and off to Newport Beach we went. Do you see a pattern developing here? This time the 45 minutes really was 45 minutes and they were very nice. We said no, and the guy said “I have 5 appointments today, 3 will buy, so if you’ll excuse me I need to be ready for buyers.” and he left.

The very next year another company called and off to San Antonio we went. This one was the worst. Three hours into the pressure cooker, threats of double charging for our free weekend if we didn’t hang around, I finally said “What is the least expensive thing we can buy to get out of here right now?”


He showed us a “trial” package that gave us two years of timeshare time, then it went away. My credit card flew out of my wallet as fast as it could and without missing a beat the salesman ran it through the machine and handed me a receipt, and said “I’ll be here when you come back to buy for good, you are going to enjoy this.”
Over the next two years we used every penny of that timeshare we could. It was supposed to be two weeks per year of a one bedroom for two years. A total of four weeks. My wife made it a challenge to get as much of our “investment” back as possible. She booked a three bedroom for a week on the east coast and we brought my whole family out. Later she booked two bedroom units in Hawaii, Orlando and Nashville. Never once did she get a one bedroom and we stretched it to over 5 weeks using a couple of off peak visits.
Each time we used to find cheap hotel rates and compare costs. The timeshare was 20% less expensive, and we had a kitchen and living room every time. Son of gun if the guy wasn’t right. We are now owners, we decided to buy in.
One argument we used for not getting a timeshare was the ownership/equity gain if you own a house. That is still a tough argument since timeshares are increasing in supply to equal demand so the likelihood of the value going up any time soon is close to zero. Disney appears to be doing a very good job of coming close though. Online pricing on the secondary market is much higher than other brands.

If you add up all of the expenses of taking care of a second home that you don’t use, a timeshare might not be a bad deal. If you don’t want the headaches of renting out your place when you aren’t using it, a time share looks better every minute. In the best case you could do both, buy a slightly smaller condo at a place you like to go for long vacations or visit frequently and get a timeshare to hit the road anytime you like.

Most of the timeshare companies have two levels of ownership. The top level is for people who purchased directly from the company and there are a host of advantages and benefits to that group. One of the biggest is being able to book earlier and get extra time or better room upgrades. If you have the ability to book vacations way in advance and have a lot of airline miles from business travel or credit card purchases, buying directly from the developer might be the way to go. The developers are of course always looking to give benefits to limit the value on the secondary market.

I guess it is possible they’ll do something different if they sell out that is. Then again who knows. I haven’t seen a property sell out yet. Once again Disney might be the closest to selling out.
The second group are the people who buy the points at half price online or from timeshare resellers. This is called the “secondary market”. In my case because I don’t normally book more than a month or two in advance, many of the top tier benefits don’t help me, so I bought my time at half price on the secondary market. If there were an “amnesty” period, or if I could buy a few more points to move my points to a higher status, I might consider it.


I can’t say for sure if it is my late booking or because I am a “secondary market class” owner but we do get the smaller corner units next to the elevator and ice machine quite often. Even so the rooms are much nicer than similar hotels in the area.
This year my wife and I have been to Hawaii, and were able to send my parents to a resort near their home when their floors were being re-finished. We already have another trip booked to Orlando in the Fall, and are looking for somewhere new and fun to go later.
Once you have the timeshare, and decide to make the best of it, they really can be a lot of fun. Once you pay off the initial purchase, the annual maintenance fees are well below the costs of a hotel from what we have seen. This year so far we have only used about half of our time and are already ahead of the game when compared to hotels in the same area.


If nothing else having the timeshare forces us to get out of the house and go somewhere else at least twice a year. It is a great way to shake loose the cobwebs and look at new business ideas and talk about our finances without all of the distractions you have at home.
We met a lady in Hawaii who normally just goes for 3 day weekends an hour from her house. She calls them her quarterly “staycations” even though she isn’t really staying home.
I have always been a proponent of a quarterly financial planning meeting from both home and business. Having a timeshare is one way to do that as well.
To steal the sales pitch from an apartment I once rented a room in, now I think of my timeshare as my “No Hassle Castle.”



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